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DE646932C - Process for the production of diamino alcohols of the fatty aromatic series - Google Patents

Process for the production of diamino alcohols of the fatty aromatic series

Info

Publication number
DE646932C
DE646932C DEC51072D DEC0051072D DE646932C DE 646932 C DE646932 C DE 646932C DE C51072 D DEC51072 D DE C51072D DE C0051072 D DEC0051072 D DE C0051072D DE 646932 C DE646932 C DE 646932C
Authority
DE
Germany
Prior art keywords
alcohols
production
aromatic series
fatty aromatic
phenyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
DEC51072D
Other languages
German (de)
Inventor
Dr Heinrich Hornstein
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
CHEMISCHE FABRIKEN DR JOACHIM
Original Assignee
CHEMISCHE FABRIKEN DR JOACHIM
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by CHEMISCHE FABRIKEN DR JOACHIM filed Critical CHEMISCHE FABRIKEN DR JOACHIM
Priority to DEC51072D priority Critical patent/DE646932C/en
Application granted granted Critical
Publication of DE646932C publication Critical patent/DE646932C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
    • C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
    • C07C215/30—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von Diaminoalkoholen der fettaromatischen Reihe Im Patent 640 582 ist ein Verfahren zur Herstellung von Abkömmlingen des optisch aktiven oder racemischen i-Phenyl-2-methylaminopropan-i-ols beschrieben, das darin besteht, daß man auf i-Phenyl=2-methylaminopropan-i-ol Dialkylaminoalkohole unter Zusatz von wasserabspaltenden Mitteln einwirken läßt.Process for the production of diamino alcohols of the fatty aromatic Series In patent 640,582 is a process for the production of descendants of the optically active or racemic i-phenyl-2-methylaminopropan-i-ols described therein consists that on i-phenyl = 2-methylaminopropan-i-ol dialkylamino alcohols under Addition of water-releasing agents can act.

In weiterer Ausbildung des Verfahrens wurde gefunden, daß man das Verfahren auch allgemein auf Monoaminoalkohole der Zusammensetzung worin R, Wasserstoff oder Aralkyl bedeutet, anwenden kann. Demgemäß werden nach der Erfindung Verbindungen dieser Zusammensetzung mit Dialkylaminoalkoholen unter Zusatz von wasserabspaltenden Mitteln, -wie z. B. Chlorzink, Phosphorpentoxyd o. dgl., behandelt.In a further development of the process, it was found that the process can also generally be applied to monoamino alcohols of the composition in which R, hydrogen or aralkyl can be used. Accordingly, according to the invention, compounds of this composition with dialkylamino alcohols with the addition of dehydrating agents, such as. B. zinc chloride, phosphorus pentoxide o. The like. Treated.

Die nach dem Verfahren gewonnenen Diaminoalkohole sollen als Heilmittel bzw. als Zwischenprodukte zur Herstellung von Heilmitteln verwendet werden. Beispiel i i-Phenyl-2-(diäthylaminoäthylbenzyl)-arninopropan-i-ol 7,2 g i-Phenyl-2-benzylaminopropan-i-ol werden in 20 g Diäthylaminoäthylalkohol gelöst und nach Zusatz von q. g Phosphorpentoxyd im geschlossenen Gefäß 30 Stunden auf 16o° erhitzt. Es wird in Wasser und Salzsäure aufgenommen, alkalisch gemacht und ausgeäthert. Nach Verjagen des Äthers wird der nicht umgesetzte Aminoalkohol im Vakuum abdestilliert, der Rückstand in Äther aufgenommen und mit ätherischer Salzsäure versetzt. Das ausfallende Produkt wird zweimal aus Alkohol mit Äther umgefällt und stellt das salzsaure Salz der gewünschten Base dar. Hygroskopische Kristalle. 16,9 °/o Cl. Berechnet 17,2 Beispiel 2 i-Phenyl-2-(diäthylaminoäthyl)-aminopropan-I-O1 18,79 . i-Phenyl-2-aminopropan-i-ol werden mit 12 g Diäthylaminoäthylalkohol gemischt und unter Zusatz von 2o g entwässertem Zinkchlorid in geschlossenem Gefäß 25 Stunden auf 16o° erhitzt. Es wird in Wasser aufgenommen, mit Salzsäure congosauer gemacht, von Verunreinigungen abfiltriert und stark alkalisch gemacht. Der alkalischen Mischung «erden durch Ausäthern die Basen entzogen. Der Äther wird verj,a4t und der Rückstand im Hochvakuum fräkt.yp.'iert. Das i-Phenyl-2-diätliylatnirioprol)-asiedet bei o,5 mm und etwa i-Io°. Da.#I` , lt .bildet farblose Kristalle von F. The diamino alcohols obtained by the process are intended to be used as medicinal products or as intermediate products in the manufacture of medicinal products. Example i i-Phenyl-2- (diethylaminoethylbenzyl) aminopropan-i-ol 7.2 g of i-phenyl-2-benzylaminopropan-i-ol are dissolved in 20 g of diethylaminoethyl alcohol and, after adding q. g of phosphorus pentoxide in a closed vessel heated to 160 ° for 30 hours. It is taken up in water and hydrochloric acid, made alkaline and etherified. After chasing off the ether, the unreacted amino alcohol is distilled off in vacuo, the residue is taken up in ether and ethereal hydrochloric acid is added. The precipitated product is reprecipitated twice from alcohol with ether and represents the hydrochloric acid salt of the desired base. Hygroscopic crystals. 16.9% Cl. Calculated 17.2 Example 2 i-Phenyl-2- (diethylaminoethyl) aminopropane-I-O1 18.79 . i-Phenyl-2-aminopropan-i-ol are mixed with 12 g of diethylaminoethyl alcohol and heated to 160 ° for 25 hours with the addition of 20 g of dehydrated zinc chloride in a closed vessel. It is taken up in water, made congo acidic with hydrochloric acid, filtered off from impurities and made strongly alkaline. The bases are removed from the alkaline mixture by etherification. The ether is verj, a4t and the The residue is fräkt.yp.'iert in a high vacuum. That i-Phenyl-2-diethylatnirioprole) -asboiled at 0.5 mm and about i-Io °. Since. # I`, according to colorless crystals from F.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Diaminoalkoholen der fettaromatischen Reihe, dadurch gekennzeichnet, daß man in Abänderung des Verfahrens des Patent 640 582 hier Dialkylaminoalkohole statt auf i-Phenyl-a-methylaminopropan-i-ol auf fettaromatische Monoaminoalkohole der Zusammensetzung worin R, Wasserstoff oder Aralkyl bedeutet, unter Zusatz von wasserabspaltenden Mitteln einwirken läßt.PATENT CLAIM: Process for the preparation of diamino alcohols of the fatty aromatic series, characterized in that, as a modification of the process of patent 640 582, dialkylamino alcohols are used instead of i-phenyl-a-methylaminopropan-i-ol on fatty aromatic monoamino alcohols of the composition in which R, hydrogen or aralkyl is allowed to act with the addition of dehydrating agents.
DEC51072D 1934-07-10 1934-07-10 Process for the production of diamino alcohols of the fatty aromatic series Expired DE646932C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEC51072D DE646932C (en) 1934-07-10 1934-07-10 Process for the production of diamino alcohols of the fatty aromatic series

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC51072D DE646932C (en) 1934-07-10 1934-07-10 Process for the production of diamino alcohols of the fatty aromatic series

Publications (1)

Publication Number Publication Date
DE646932C true DE646932C (en) 1937-06-24

Family

ID=7027312

Family Applications (1)

Application Number Title Priority Date Filing Date
DEC51072D Expired DE646932C (en) 1934-07-10 1934-07-10 Process for the production of diamino alcohols of the fatty aromatic series

Country Status (1)

Country Link
DE (1) DE646932C (en)

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